Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 30, Pages 5962-5966Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101029
Keywords
Lewis acids; Cycloaddition; NMR spectroscopy; Kinetics
Categories
Funding
- Deutsche Forschungsgemeinschaft
- Millennium Pharmaceuticals, Inc., Cambridge, U.S.A
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The quantification of Lewis acidity is accomplished by a deuterated quinolizidine probe utilizing H-2 NMR spectroscopy. The chemical shifts of the H-2 NMR signals for aluminum, boron, titanium, and zinc halides are reported. The rate constants for Lewis acid catalyzed reactions were determined by utilizing UV/Vis spectroscopy for Diels-Alder and Povarov reactions under pseudo-first-order conditions. The magnitude of the H-2 NMR chemical shifts correlates with the rate constants of the organic transformations for many Lewis acids investigated in the same order, whereas some deviations are identified.
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